Robert Massé

Aminoglycoside antibiotics: Studies directed toward the selective modification of hydroxyl groups: Synthesis of 3′-epiparomamine and 3′-epineamine

Based on the knowledge that certain bacterial strains can produce enzymes that are capable of phosphorylating the 3′-hydroxyl group of a series of aminoglycoside antibiotics, the pseudodisaccharide 3′-epiparomamine was prepared through a series of high yieldingsteps, starting from paromamine. Application of selective halogenation and subsequent animation reactions allowed the efficient transformation of 3′-epiparomamine to 3′-epineamine. The two compounds were not substrates for the inactivating enzymes, however, they are also much weaker antibiotics compared to the parent compounds paromamine and neamine. Model synthetic studies in the 2-amino-2-deoxy-D-ghicose series are also reported.

Synthetic approaches to kasugamine

Abstract Reactions are described that lead to an immediate, chemical precursor of kasugamine the amino-sugar component of the aminocyclitol antibiotic kasugamycin. The key reaction involved the introduction of a bromine atom by a stereoselective ring-opening of a benzylidene acetal.